Title: South Side Vacation Home Rentals from CA $205: Search Top Private Vacation Homes for Rent | Expedia.ca

 

[South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides)

![Chicago, IL featuring interior views and an airport as well as a couple](https://images.trvl-media.com/place/5719117/eadab43c-a88e-4198-bdcd-703715c2ebbd.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by by Midway Intl Airport

# South Side Vacation Rentals

-   ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)
    
    ### 
    
    Change your mind
    
    Book hotels with free cancellation
    
-   ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)
    
    ### 
    
    Treat yourself
    
    Sign in to save 10% or more on thousands of hotels
    
    [Sign in](https://www.expedia.ca/login)
    
-   ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)
    
    ### 
    
    Be picky
    
    Search almost a million properties worldwide
    

## Check prices for these dates

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select South Side Vacation Homes

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/b1ada0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/48a5d932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/d8580e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/6a00edbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sauk Village

10/10

Exceptional

(1)

"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aaron K.

CA $129

CA $205 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Sauk-Village-Hotels-Pleasant-3-Bedroom-House-In-Sauk-Village.h121815186.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/9d278ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/5b7a273e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/138bf941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/3c3ca737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Richton Park

9.0/10

Wonderful

(13)

"Awesome stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patrick J.

CA $151

CA $436 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Richton-Park-Hotels-Spacious-3br-Home-Near-Chicago.h108885786.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w506h639x259y44-83e61931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w505h683x260y0-7687ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/f64972cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w508h683x259y0-938c1ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gary

CA $182

CA $588 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Gary-Hotels-Honeycomb-Hideout-W-2-Bedrooms.h88178891.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e79449bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/dfa31946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/f18fcae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/5ccfbbbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Robertsdale

9.8/10

Exceptional

(15)

"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen D.

CA $200

CA $279 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Whiting-Hotels-Charming-3-BR-Home-On-A-Cobblestone-Street-Near-The-Lake-Michigan-Lakefront.h108219403.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/7374e6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/327a76af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/7ff9f215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/b86200c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Miller Beach

9.8/10

Exceptional

(36)

"We loved our stay and had a relaxing time in the area. Buying groceries to cook was great with a full kitchen to cook with. Rooms were super nice and also had every accommodation we could need. Definitely will be looking to stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Braden S.

CA $119

CA $429 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Gary-Hotels-Dunes-Escape-Minutes-From-Indiana-Dunes-National-Park.h83025813.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/a0f5c46e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/49bef28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/1dc70e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/c1640248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Worth

9.6/10

Exceptional

(53)

"Perfect place for an 8 person golf trip! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Griffin P.

CA $217

CA $463 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/84ad0fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/485e4f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/0a83dc4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/2e3f2077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Miller Beach

10/10

Exceptional

(1)

"Lovely, relaxing and clean. Host is very responsive. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer L.

CA $133

CA $467 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Gary-Hotels-Spacious-3BR-House-With-Firepit-And-Grill.h118254007.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/48e46ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/9a820eca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/6a1f9864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/31d65898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lockport

10/10

Exceptional

(4)

"Amazing property had everything we need! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rachel

CA $245

CA $530 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Lockport-Hotels-Lockport-Haven3-King-BedsWi-FiNear-Downtown.h116470311.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/24b80113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/58bc029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/d13cd0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/f6aa2476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Des Plaines

9.0/10

Wonderful

(4)

"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie G.

CA $97

CA $389 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Getaway-Near-ORD-With-Great-Local-Amenities.h89818126.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w867h654x78y17-d683a7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/ad61d9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w904h683x60y0-33f7d28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/9878af78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Willow Springs

8.8/10

Excellent

(15)

"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gabriela N.

CA $252

CA $556 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Coziest-Estate-Home-20-Minutes-To-Downtown.h88494875.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/aa9396b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/699d0fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/33378924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/3f6e4959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Oak Park

10/10

Exceptional

(12)

"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas P.

CA $192

CA $646 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Vintage-Urban-Retreat.h105136524.Hotel-Information)

![Fitness facility](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/c9a94206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/2246e8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/33260724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/6b52890f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Belmont Cragin

CA $133

CA $770 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Chicago-Hotels-Theater-Game-Room-Gym-Firepit-4BR-Home.h122811987.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/e376d974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/dc90b17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/08f64820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/190b2201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Maywood

7.8/10

Good

(15)

"Very nice place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elliot H.

CA $208

CA $339 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/ff3980a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/b3ebc668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/139732fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/f670e4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Miller Beach

CA $182

CA $452 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Gary-Hotels-Cozy-Family-Getaway-4-Blocks-Or-A-9-Minute-Walk-To-The-Beach.h117462645.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/1e6ca815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/ccf123af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/5ff1a0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/w2874h1613x0y1-952d9d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Elmhurst

8.8/10

Excellent

(38)

"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott C.

CA $220

CA $481 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-LUXE-3-BR.h96384152.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/bf01096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/w1096h1452x0y0-f7b35f5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/45b7296c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/5e34eeff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wheaton

10/10

Exceptional

(54)

"Great place for a family visit to Wheaton! Thanks!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa

CA $238

CA $431 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Charming-Cottage-Close-To-CollegeTownStation.h74243056.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/267c108a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/b071d2aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, Hulu, books](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/b02b5cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/3706aabf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lisle

9.6/10

Exceptional

(19)

"Convenient location to family that lives in the area"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea G.

CA $147

CA $374 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Chicago-Hotels-VERY-Close-To-Colleges.h76925599.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/010eed58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/w912h683x56y0-90e9213c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/56333a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/7448b12a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gary

8.6/10

Excellent

(17)

"i had a good time here. the house was great. thank you"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alvaro C.

CA $225

CA $625 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Gary-Hotels-Theater-RMKG-BdFam-Friendly-Home-NR-DunesBeach.h102515612.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/696abe25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/392f7166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/7bc6fa05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/6b638712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wood Dale

10/10

Exceptional

(17)

"Great property and great host!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Darin H.

CA $250

CA $550 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Chicago-Hotels-King-Bed.h71947955.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/a03596e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/fcb2b3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/a531c8c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/cd881412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gary

10/10

Exceptional

(4)

"Very nice property. Kids loved staying here! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sydney D.

CA $284

CA $627 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Gary-Hotels-COMFORTABLE-ALLUSION.h111668679.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-16&endDate=2025-12-17&regionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

Black Friday Sale

Limited-time deals: save up to 50% on select hotels

[Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_553248635074842823)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=COTTAGE)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=VACATION_HOME)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-02&d1=2026-03-02&endDate=2026-03-05&d2=2026-03-05&lodging=RESIDENCE)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Private-Vacation-Homes.d553248635074842823-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Private-Vacation-Homes.d553248635074842823-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top South Side Hotel Reviews

![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg)

### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent

"The need to stay in Chicago overnight was unplanned so finding the room clean and looking comfortable right away made my stress level come down"

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information)

![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg)

### Sophy Hyde Park

10/10 Excellent

"Very nice room and amenities. We enjoy the atmosphere in the lobby!!"

[](https://expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information)

![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg)

### Chicago Marriott Midway

10/10 Excellent

"Very convenient and clean and friendly! "

[](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information)

![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg)

### Motel 6 - Chicago, IL

10/10 Excellent

"Grest"

[](https://expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information)

![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg)

### Jaslin Hotel

10/10 Excellent

"Excellent- we were able to check out late for a small fee"

[](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information)

![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg)

### Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"As always fabulous experience. Great customer service."

[](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information)

![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg)

### Best Western Inn & Suites - Midway Airport

10/10 Excellent

"Hotel and room was very clean and the desk clerk was courteous "

[](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information)

![Saratoga Motel By Capital O Near Midway Airport Chicago IL](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3451h2304x0y0-39d39828_y.jpg)

### Saratoga Motel By Capital O Near Midway Airport Chicago IL

10/10 Excellent

"Room was spotless "

[](https://expedia.ca/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information)

![Best Motel By OYO Chicago I-90](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/19cdbb10_y.jpg)

### Best Motel By OYO Chicago I-90

8/10 Good

"Clean room "

[](https://expedia.ca/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information)

## Find out more about South Side

## South Side Vacation Homes information

| Number of reviews | 270 |
| --- | --- |
| Accommodation | 97 Vacation Homes |
| Lowest Price | CA $205 |
| Highest Price | CA $770 |

## Explore a world of travel with Expedia

-   Lodging
-   Flights
-   Packages
-   Cars
-   More ways to book

-   [Cheap Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Cheap-Hotels.0-n6132245-0-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Family Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Family-Hotel.0-n6132245-0-tFamilyHotel.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Luxury-Hotel.0-n6132245-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Bronzeville Hotels](https://www.expedia.ca/Bronzeville-Chicago-Hotels.0-n6132245-0.Travel-Guide-Filter-Hotels)
-   [Canaryville Hotels](https://www.expedia.ca/Canaryville-Chicago-Hotels.0-n6132307-0.Travel-Guide-Filter-Hotels)
-   [Aparthotels in Cermak-Chinatown Station](https://www.expedia.ca/Cermak-Chinatown-Station-Apart-Hotels.d6210889-aaApartHotels.Travel-Guide-Accommodation)
-   [Aparthotels in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Apart-Hotels.d6213376-aaApartHotels.Travel-Guide-Accommodation)
-   [Chalets in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Chalets.d6213376-aaChalets.Travel-Guide-Accommodation)
-   [Inns in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Inns.d6213376-aaInns.Travel-Guide-Accommodation)
-   [Resorts in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Resort-Hotels.d6213376-aaResortHotels.Travel-Guide-Accommodation)
-   [B&B in Chicago 47th Street Station](https://www.expedia.ca/Chicago-47th-Street-Station-Bed-And-Breakfast.d6212783-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Hotels near Chicago 47th Street Station](https://www.expedia.ca/Chicago-47th-Street-Station-Hotels.d6212783.Travel-Guide-Hotels)
-   [Guest Houses in Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Guest-Houses.d6212787-aaGuestHouses.Travel-Guide-Accommodation)
-   [Hotels near Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Hotels.d6212787.Travel-Guide-Hotels)
-   [Resorts in Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Resort-Hotels.d6212787-aaResortHotels.Travel-Guide-Accommodation)
-   [Guest Houses in Chicago 55th-56th-57th Street Station](https://www.expedia.ca/Chicago-55th-56th-57th-Street-Station-Guest-Houses.d6212797-aaGuestHouses.Travel-Guide-Accommodation)
-   [Hotels near Chicago 55th-56th-57th Street Station](https://www.expedia.ca/Chicago-55th-56th-57th-Street-Station-Hotels.d6212797.Travel-Guide-Hotels)
-   [Resorts in Chicago 55th-56th-57th Street Station](https://www.expedia.ca/Chicago-55th-56th-57th-Street-Station-Resort-Hotels.d6212797-aaResortHotels.Travel-Guide-Accommodation)
-   [Hotels near Chicago 59th Street Station](https://www.expedia.ca/Chicago-59th-Street-Station-Hotels.d6212800.Travel-Guide-Hotels)
-   [Inns in Chicago 59th Street Station](https://www.expedia.ca/Chicago-59th-Street-Station-Inns.d6212800-aaInns.Travel-Guide-Accommodation)
-   [Guest Houses in Chicago 63rd Street Station](https://www.expedia.ca/Chicago-63rd-Street-Station-Guest-Houses.d6212802-aaGuestHouses.Travel-Guide-Accommodation)
-   [Guest Houses in Chicago 79th Street Station](https://www.expedia.ca/Chicago-79th-Street-Station-Guest-Houses.d6212914-aaGuestHouses.Travel-Guide-Accommodation)
-   [Inns in Chicago Halsted Station](https://www.expedia.ca/Chicago-Halsted-Station-Inns.d6213464-aaInns.Travel-Guide-Accommodation)
-   [Resorts in Chicago Halsted Station](https://www.expedia.ca/Chicago-Halsted-Station-Resort-Hotels.d6213464-aaResortHotels.Travel-Guide-Accommodation)
-   [Chicago Hotels](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)
-   [Aparthotels in Chicago McCormick Place Station](https://www.expedia.ca/Chicago-McCormick-Place-Station-Apart-Hotels.d6212776-aaApartHotels.Travel-Guide-Accommodation)
-   [B&B in Chicago McCormick Place Station](https://www.expedia.ca/Chicago-McCormick-Place-Station-Bed-And-Breakfast.d6212776-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Guest Houses in Chicago McCormick Place Station](https://www.expedia.ca/Chicago-McCormick-Place-Station-Guest-Houses.d6212776-aaGuestHouses.Travel-Guide-Accommodation)
-   [Hostels in Chicago McCormick Place Station](https://www.expedia.ca/Chicago-McCormick-Place-Station-Hostels.d6212776-aaHostels.Travel-Guide-Accommodation)
-   [Inns in Chicago McCormick Place Station](https://www.expedia.ca/Chicago-McCormick-Place-Station-Inns.d6212776-aaInns.Travel-Guide-Accommodation)
-   [Resorts in Chicago McCormick Place Station](https://www.expedia.ca/Chicago-McCormick-Place-Station-Resort-Hotels.d6212776-aaResortHotels.Travel-Guide-Accommodation)
-   [Hotels near Chicago Museum of Science and Industry](https://www.expedia.ca/Chicago-Museum-Of-Science-And-Industry-Hotels.0-l6064043-0.Travel-Guide-Filter-Hotels)
-   [B&B in Chicago South Shore Station](https://www.expedia.ca/Chicago-South-Shore-Station-Bed-And-Breakfast.d6212824-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Inns in Chicago Stony Island Station](https://www.expedia.ca/Chicago-Stony-Island-Station-Inns.d6212811-aaInns.Travel-Guide-Accommodation)
-   [Hotels near Cottage Grove Station](https://www.expedia.ca/Cottage-Grove-Station-Hotels.d6211061.Travel-Guide-Hotels)
-   [Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels)
-   [Hotels near DuSable Museum of African-American History](https://www.expedia.ca/DuSable-Museum-Of-African-American-History-Hotels.0-l6065113-0.Travel-Guide-Filter-Hotels)
-   [East Hyde Park Hotels](https://www.expedia.ca/East-Hyde-Park-Chicago-Hotels.0-n553248635976384151-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Garfield Station](https://www.expedia.ca/Garfield-Station-Hotels.d6210926.Travel-Guide-Hotels)
-   [Inns in Garfield Station](https://www.expedia.ca/Garfield-Station-Inns.d6210926-aaInns.Travel-Guide-Accommodation)
-   [Adults Only Resorts & in Grand Boulevard](https://www.expedia.ca/Grand-Boulevard-Chicago-Hotels-Adults-Only-Resorts.0-n6132310-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [Grand Boulevard Hotels](https://www.expedia.ca/Grand-Boulevard-Chicago-Hotels.0-n6132310-0.Travel-Guide-Filter-Hotels)
-   [B&B in Halsted Station](https://www.expedia.ca/Halsted-Station-Bed-And-Breakfast.d6211063-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [All Inclusive Resorts and in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n117842-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
-   [Beach Hotel Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Beach-Hotel.0-n117842-0-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Boutique Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Boutique-Hotel.0-n117842-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Cheap-Hotels.0-n117842-0-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Family Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Family-Hotel.0-n117842-0-tFamilyHotel.Travel-Guide-Filter-Hotels)
-   [Historic Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Historic-Hotel.0-n117842-0-tHistoricHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with Early Check-in in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Hotel-With-Early-Check-In.0-n117842-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels)
-   [Hotels with an Indoor Pool in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n117842-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
-   [Hotels with Kitchenettes in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Hotels-With-Kitchenettes.0-n117842-0-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels)
-   [Hyatt Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Hyatt-Hotels.0-n117842-0--bHyattHotels.Travel-Guide-Filter-Hotels)
-   [La Quinta Inn & Suites Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-La-Quinta-Inn-Suites.0-n117842-0--bLaQuintaInnSuites.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Luxury-Hotel.0-n117842-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Oceanfront Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Oceanfront-Hotels.0-n117842-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Pet-Friendly-Hotel.0-n117842-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Spa-Hotel.0-n117842-0-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Hyde Park Hotels](https://www.expedia.ca/Hyde-Park-Chicago-Hotels.0-n117842-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Hyde Park Hair Salon](https://www.expedia.ca/Hyde-Park-Hair-Salon-Hotels.0-l553248621533116334-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Ida B Wells House](https://www.expedia.ca/Ida-B-Wells-House-Hotels.0-l553248621533116338-0.Travel-Guide-Filter-Hotels)
-   [Vacation Homes in Indiana Station](https://www.expedia.ca/Indiana-Station-Private-Vacation-Homes.d6211032-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Cheap Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Cheap-Hotels.0-n6132343-0-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Luxury-Hotel.0-n6132343-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Spa-Hotel.0-n6132343-0-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Kenwood Hotels](https://www.expedia.ca/Kenwood-Chicago-Hotels.0-n6132343-0.Travel-Guide-Filter-Hotels)
-   [B&B in King Drive Station](https://www.expedia.ca/King-Drive-Station-Bed-And-Breakfast.d6211057-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Hotels near King Drive Station](https://www.expedia.ca/King-Drive-Station-Hotels.d6211057.Travel-Guide-Hotels)
-   [Hotels near Midway Plaisance](https://www.expedia.ca/Midway-Plaisance-Hotels.0-l6069199-0.Travel-Guide-Filter-Hotels)
-   [Boutique Hotels in Oakland](https://www.expedia.ca/Oakland-Chicago-Hotels-Boutique-Hotel.0-n6132392-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Oakland](https://www.expedia.ca/Oakland-Chicago-Hotels-Luxury-Hotel.0-n6132392-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Oakland](https://www.expedia.ca/Oakland-Chicago-Hotels-Spa-Hotel.0-n6132392-0-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Oakland Hotels](https://www.expedia.ca/Oakland-Chicago-Hotels.0-n6132392-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Oriental Institute Museum](https://www.expedia.ca/Oriental-Institute-Museum-Hotels.0-l6069227-0.Travel-Guide-Filter-Hotels)
-   [Resorts in Roosevelt Station](https://www.expedia.ca/Roosevelt-Station-Resort-Hotels.d6210882-aaResortHotels.Travel-Guide-Accommodation)
-   [Villas in Roosevelt Station](https://www.expedia.ca/Roosevelt-Station-Villas.d6210882-aaVillas.Travel-Guide-Accommodation)
-   [Cabin Rentals in Southwest Side](https://www.expedia.ca/Southwest-Side-Cabins.d553248635976475403-aaCabins.Travel-Guide-Accommodation)
-   [Hotels near University of Chicago](https://www.expedia.ca/University-Of-Chicago-Hotels.0-l6064081-0.Travel-Guide-Filter-Hotels)
-   [Hotels near University of Chicago Medicine](https://www.expedia.ca/University-Of-Chicago-Medicine-Hotels.0-l553248635389801569-0.Travel-Guide-Filter-Hotels)
-   [All Inclusive Resorts and in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n171466-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
-   [Boutique Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Boutique-Hotel.0-n171466-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Cheap-Hotels.0-n171466-0-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Luxury-Hotel.0-n171466-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Washington Park Hotels](https://www.expedia.ca/Washington-Park-Chicago-Hotels.0-n171466-0.Travel-Guide-Filter-Hotels)
-   [Washington Park Court Hotels](https://www.expedia.ca/Washington-Park-Court-Chicago-Hotels.0-n6132200-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Washington Park](https://www.expedia.ca/Washington-Park-Hotels.0-l507383-0.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Woodlawn](https://www.expedia.ca/Woodlawn-Chicago-Hotels-Cheap-Hotels.0-n6132422-0-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Hotels with an Indoor Pool in Woodlawn](https://www.expedia.ca/Woodlawn-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n6132422-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Woodlawn](https://www.expedia.ca/Woodlawn-Chicago-Hotels-Luxury-Hotel.0-n6132422-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Woodlawn Hotels](https://www.expedia.ca/Woodlawn-Chicago-Hotels.0-n6132422-0.Travel-Guide-Filter-Hotels)

-   [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
-   [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

-   [Visit Canaryville](https://www.expedia.ca/Chicago-Canaryville.dx6132307)
-   [Visit Fuller Park](https://www.expedia.ca/Chicago-Fuller-Park.dx6132374)
-   [Visit Indian Village](https://www.expedia.ca/Chicago-Indian-Village.dx553248635976382922)
-   [Chicago Museum of Science and Industry](https://www.expedia.ca/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
-   [Obama's House](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction)
-   [Robie House](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction)

-   [Car rentals near Hyde Park](https://www.expedia.ca/Car-Rentals-In-Hyde-Park.d117842.Car-Rental-Guide)
-   [Hertz Rental Cars in Hyde Park](https://www.expedia.ca/Hertz-Car-Rentals-In-Hyde-Park.d117842-c40.Car-Rental-Guide-Suppliers)

-   [Book Vacation Homes in South Side on Expedia.com](https://www.expedia.com/South-Side-Private-Vacation-Homes.d553248635074842823-aaPrivateVacationHomes.Travel-Guide-Accommodation)